tell us more about Outlook's reign over the Eastern seas
Outlook only cares about one thing in life, furthering his family name. He was a cruel man who never should have become King but likely only did so because he was a powerful witch or... maybe he payed some nasty eels to take care of his competition.
He obviously favored those from a noble or royal blood like his. Anyone else was cast out to make the sea he controlled more attractive to those with a higher status than his. He still had his trading company until his death and definitely shipped off and sold members of his own kingdom to gain favor. They were all undesirables to him anyway-- and now he doesn't have to watch the filth tarnish his streets and he gets to suck up to people he’d want to marry Sabo off to.
Sabo despises everything, but he’s only ten or eleven so what can he really do? He can only ruin so many meetings for possible marriages before Outlook just stops bringing him. Locks him up and then just simply tells those royals about him instead of trying to show him off.
Outlooks got strong magic so they’d know good and well that Sabo does too. Stelly has magic too but it isnt anywhere near as good, so he’s a bit harder to sell off even if he is more cooperative.
Outlook would also threaten and straight up force people from their homes to make way for bigger and better stuff. He knows everyone counts on the wards to protect the whole kingdom but he’s the one who made them... he can control what they actually protect and leave certain areas open to attacks from say.. creatures like Bluejam.
Probably only those in the castle would have even tried to protect Outlook once WB came.